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Merck
CN

393193

Hydrocinnamaldehyde

technical grade, 90%

Synonym(s):

3-Phenylpropionaldehyde

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About This Item

Linear Formula:
C6H5CH2CH2CHO
CAS Number:
104-53-0
Molecular Weight:
134.18
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24864504
EC Number:
203-211-8
Beilstein/REAXYS Number:
1071910
MDL number:
MFCD00007021

Key Documents

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Product Name

Hydrocinnamaldehyde, technical grade, 90%

InChI key

YGCZTXZTJXYWCO-UHFFFAOYSA-N

InChI

1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6,8H,4,7H2

SMILES string

[H]C(=O)CCc1ccccc1

grade

technical grade

assay

90%

form

liquid

impurities

<5% 3-phenyl-1-propanol

refractive index

n20/D 1.523 (lit.)

bp

97-98 °C/12 mmHg (lit.)

density

1.019 g/mL at 25 °C (lit.)

functional group

aldehyde
phenyl

Quality Level

100

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Application

Hydrocinnamaldehyde may be used in the synthesis of the following:
  • 2-Chloro hydrocinnamaldehyde by α-chlorination.
  • Mixture of homopropargyl alcohols by kinetic resolution-allenylboration reactions.
  • Mixture of syn- and anti-β-hydroxyallylsilanes by hydroboration of allenylsilane.
  • (2S)-2-Hydroxy-4-phenylbutanenitrile by catalytic asymmetric cyanosilylation.
  • Cinnamaldehyde by dehydrogenation reaction using Pd(TFA)2/4,5-diazafluorenone catalyst.

General description

Hydrocinnamaldehyde is C=C double bond hydrogenated cinnamaldehyde. It has been synthesized by the selective hydrogenation of C=C double bond of cinnamaldehyde by various methods. Hydrocinnamaldehyde and nitromethane undergoes Henry reaction to form nitroaldols. The C1 and C3 position labelled with 13C of hydrocinnamaldehyde was subjected to mass spectrometry and the fragmentation pattern was elucidated.

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

203.0 °F - closed cup

flash_point_c

95 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2072
STBJ9340
STBJ5884
STBJ4050
STBG7939

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Hydrogenation of cinnamaldehyde using catalysts prepared from supported palladium phosphine complexes.
Cairns GR, et al
J. Catal., 166(1), 89-97 (1997)
Enantioselective henry reactions under dual Lewis acid/amine catalysis using chiral amino alcohol ligands.
Claudio Palomo et al.
Angewandte Chemie (International ed. in English), 44(25), 3881-3884 (2005-05-14)
Catalytic selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde.
Zhang Y, et al
Applied Catalysis A: General, 192(2), 247-251 (2000)
Tianning Diao et al.
Chemical science, 3, 887-891 (2012-06-13)
The direct α, β-dehydrogenation of aldehydes and ketones represents an efficient alternative to stepwise methods to prepare enal and enone products. Here, we describe a new Pd(TFA)(2)/4,5-diazafluorenone dehydrogenation catalyst that overcomes key limitations of previous catalyst systems. The scope includes
Influence of Preparation Modes on Pt-Ni/CNTs Catalysts Used in the Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde.
Li Y, et al
Catalysis Letters, 126(3-4), 280-285 (2008)
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